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Kyle Tsai

The story so far

I started out as a product manager in semiconductors back in Taiwan. Most days were spent going through tech specs and figuring out what should go into the next product sprint.

Somewhere along the way, I was naïve enough to think I should have a go at building something of my own. That turned into an AI company in the F&B industry, before the ChatGPT era. We were using AI for things people thought you needed years of experience to do. We eventually sold it. I learned a lot going through that whole cycle, including how often you have to make a call before you feel ready.

London, UK (not the Ontario one, sorry) was where I switched sides of the table, joining Telefónica to focus on AI and deep tech. I worked with companies including Perplexity and ElevenLabs, and spent a lot of time helping founders navigate big companies. Getting someone excited about a technology and getting them to buy it can be quite different conversations.

At OMERS Ventures, I look across the AI tech stack, from silicon and compute infrastructure to models and applications. I usually start with where the technology is heading and what’s missing along the way. Then I start wondering what could make the whole idea unnecessary. A company can beat its competitors and still be made obsolete by something happening somewhere else. I like founders who think about that too, and who have a view on what their company could become beyond the thing they’re building today.

What should founders know about you?

I read a lot and like trying things myself. I’m usually happier reading a paper or playing with a GitHub repo than sending another “would love to connect” message.

By the time we talk, I’d like to have something to bring to the conversation. Some of my favourite meetings have ended up with a pen and paper, pulling apart an idea together. I want you to get something out of our time too.

There’s a lot we can build now. I’m curious about why you’ve chosen this particular thing, what you’ve understood about the problem, and where you think it could go.

You don’t have to be fundraising. If you’ve spent real time thinking about the problem, I’m happy to compare notes. You can absolutely still be working out the answer.

What do you like spending time thinking about?

I keep coming back to why we do things the way we do. Sometimes there’s a good reason. Sometimes the reason disappeared a while ago and everyone just carried on.

Technology changes what’s possible, but people don’t immediately change how they think or work. I find that gap interesting. What would we do differently if we weren’t starting from the way things already are?

I also wonder how much of what we call experience is understanding, and how much is knowing a pattern that happened to work before. That’s something I try to keep in mind when I’m getting a little too comfortable with my own view.

Writing helps me work through all of this. It’s where I find out whether I have an actual point, or just another long conversation going on in my head.

What do you do when you’re not working?

I’m a certified sommelier, so wine is a serious hobby that occasionally pretends to be professional development.

I also like hiking, reading and following research rabbit holes much further than I originally planned. Still slowly becoming more Canadian: learning golf, trying to stay upright on skis and wondering when winter starts to feel normal.

And I’m practising JOMO, the joy of missing out. Apparently, I don’t have to try everything or be everywhere just because I can. Still working on that.